Sodium Bis(trimethylsily)amide and Lithium Diisopropylamide in Deprotection of Alkyl Aryl Ethers: α-Effect of Silicon

Journal of Organic Chemistry

Volumn 62, Issue 12, 1997, Pages 4097-4104

  Hwu, Jih Ru ^a,b   Wong, Fung Fuh ^a   Huang, Jiann Jyh ^a   Tsay, Shwu Chen ^b  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b INSTITUTE OF CHEMISTRY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001213177     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961191k     Document Type: Article

References (50)

1. Fieser, F.; Fieser, L. F. Reagents for Organic Synthesis; John Wiley: New York, 1974; Vol. 4, p 298.
2. Fieser, F.; Fieser, L. F. Reagents for Organic Synthesis; John Wiley: New York, 1967; Vol. 1, p 1046.
3. Hwu, J. R.; Wetzel, J. M. J. Org. Chem. 1985, 50, 3946.
4. Hwu, J. R.; Chua, V.; Schroeder, J. E.; Barrans, R. E., Jr.; Khoudary, K. P.; Wang, N.; Wetzel, J. M. J. Org. Chem. 1986, 51, 4731.
5. Hwu, J. R.; Leu, L.-C.; Robl, J. A.; Anderson, D. A.; Wetzel, J. M. J. Org. Chem. 1987, 52, 188.
6. Hwu, J. R.; Robl, J. A.; Wang, N.; Anderson, D. A.; Ku, J.; Chen, E. J. Chem. Soc., Perkin Trans, 1 1989, 1823.
7. Hwu, J. R.; Anderson, D. A.; Wang, N.; Buchner, M. M.; Gani, P.; Tsay, S.-C. Chem. Ber. 1990, 123, 1667.
8. Hwu, J. R.; Tsay, S.-C. J. Org. Chem. 1990, 55, 5987.
9. Shiao, M.-J.; Ku, W.-S.; Hwu, J. R. Heterocycles 1993, 36, 323.
10. Hwu, J. R.; Jain, M. L.; Tsay, S.-C.; Hakimelahi, G. H. J. Chem. Soc., Chem. Commun. 1996, 545.
11. Hwu, J. R.; Jain, M. L.; Tsay, S.-C.; Hakimelahi, G. H. Tetrahedron Lett. 1996, 37, 2035.
12. Cuvigny, T.; Normant, H. J. Organomet. Chem. 1973, 55, 41.
13. Bhatt, M. V.; Kulkarni, S. U. Chem. Rev. 1983, 83, 249.
14. For the properties of DMEU, see: (a) Fieser, F.; Fieser, L. F. Reagents for Organic Synthesis: John Wiley: New York, 1984; Vol. 11, p 202. (b) Barker, B. J.; Rosenfarb, J.; Caruso, J. A. Angew. Chem., Int. Ed. Engl. 1979, 18, 503.
15. For the properties of DMEU, see: (a) Fieser, F.; Fieser, L. F. Reagents for Organic Synthesis: John Wiley: New York, 1984; Vol. 11, p 202. (b) Barker, B. J.; Rosenfarb, J.; Caruso, J. A. Angew. Chem., Int. Ed. Engl. 1979, 18, 503.
16. Oi, R.; Shimakawa, C.; Takenaka, S. Chem. Lett. 1988, 899.
17. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; John Wiley: New York, 1991; (a) pp 145-149; (b) pp 156-158; (c) pp 170-172 and references cited therein.
18. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; John Wiley: New York, 1991; (a) pp 145-149; (b) pp 156-158; (c) pp 170-172 and references cited therein.
19. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; John Wiley: New York, 1991; (a) pp 145-149; (b) pp 156-158; (c) pp 170-172 and references cited therein.
20. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; John Wiley: New York, 1991; (a) pp 145-149; (b) pp 156-158; (c) pp 170-172 and references cited therein.
21. Blankespoor, R. L.; Smart, R. P.; Batts, E. P.; Kiste, A. A.; Lew, R. E.; Vliet, M. E. V. J. Org. Chem. 1995, 60, 6852.
22. Loubinoux, B.; Coudert, G.; Guillaumet, G. Synthesis 1980, 638.
23. Haslam, E. In Protective Groups in Organic Synthesis; McOmie, J. F. W., Ed.; Plenum: New York, 1973; p 157 and references cited therein.
24. Kocienski, P. J. Protecting Groups; Georg Thieme Verlag: Stuttgart, 1994.
25. Haslam, E.; Haworth, R. D. J. Chem. Soc. 1955, 827.
26. Brinkman, E. A.; Berger, S.; Brauman, J. I. J. Am. Chem. Soc. 1994, 116, 8304.
27. Kawamura, T.; Kochi, J. K. J. Am. Chem. Soc. 1972, 94, 648.
28. Colvin, E. W. Silicon in Organic Synthesis; Butterworth: London, 1981; p 12.
29. Yukio, N.; Teiji, T.; Tsuneo, H. Makromol. Chem. 1989, 190, 1855.
30. Takahashi, O.; Morihashi, K.; Kikuchi, O. Bull. Chem. Soc. Jpn. 1991, 64, 1178.
31. Bassindale, A. R.; Taylor, P. G. In The Chemistry of Functional Groups: The Chemistry of Organic Silicon Compounds', Patai, S., Rappoport, Z., Eds.; John Wiley: Chichester, 1989; Part 2, p 893 and references cited therein.
32. Weber, W. P. Silicon Reagents for Organic Synthesis; Springer-Verlag: Berlin, 1983; Chapter 6, p 59.
33. Colvin, E. W. Chem. Soc. Rev. 1978, 7, 15.
34. Paquette, L. A. Science 1982, 217, 793.
35. Fleming, I. Chem. Soc. Rev. 1981, 10, 83.
36. Krief, A. Tetrahedron 1980, 36, 2531.
37. Grimm, D. T.; Bartmess, J. E. J. Am. Chem. Soc. 1902, 114, 1227 and references cited therein.
38. Rao, K. V.; Chattopadhyay, S. K. J. Org. Chem. 1990, 55, 1427.
39. Kozuka, S.; Kikuchi, A.; Yamaguchi, S. Bull. Chem. Soc. Jpn. 1981, 54, 307.
40. (a) Its physical properties and spectroscopic characteristics are consistent with those of authentic samples available from Aldrich Chemical Co.
41. (b) Aldrich Catalog Handbook of Fine Chemicals 1996-1997; Aldrich Chemical Co: Milwaukee, WI, 1996.
42. Otto, D.; Helmut, C.; Helmut, G. Liebigs Ann. Chem. 1982, 1836.
43. Loic, R.; Simone, R.; Pierre, D.; Rene, R.; Raymond, C. Eur. J. Med. Chem. Chim. Ther. 1979, 14, 281.
44. Pelizzetti, E.; Mentasti, E.; Pramauro, E. J. Chem. Soc., Perkin Trans, 2 1978, 620.
45. Carvalho, C. F.; Sargent, M. V. J. Chem. Soc., Chem. Commun. 1984, 227.
46. Maissant, J. M.; Bouchoule, C.; Blanchard, M. J. Mol. Catal. 1982, 14, 333.
47. Nolte, D. J. J. Insect. Physiol. 1976, 22, 833; Chem. Abstr. 1976, 85, 156902m.
48. Nolte, D. J. J. Insect. Physiol. 1976, 22, 833; Chem. Abstr. 1976, 85, 156902m.
49. Kidwell, R. L.; Murphy, M.; Darling, S. D. Org. Synth. 1969, 49, 90.
50. Abramovitch, R. A.; Alvernhe, G.; Bartnik, R.; Dassanayake, N. L.; Inbasekaran, M. N.; Kato, S. J. Am. Chem. Soc. 1981, 103, 4558.